[5] The first white settler in the area was William Offield, earlier of Tennessee, who arrived in 1821 with his wife Jennie (née Laughlin) and one child and settled near the confluence of Offield Creek and Sugar Creek, about five miles (8.0 km) southwest of present Crawfordsville.

It was formed from parts of Wabash New Purchase attached to Parke and Putnam Counties.

[7] Beginning on December 24, 1824, a large land sale was held for several days at the United States Land Office on Crawfordville's North Water Street, during which a large number of the area's tracts were sold at auction.

The money raised from the sale, mostly in the form of gold and silver, was packed into kegs, hauled by wagon to Louisville, carried by boat up the Ohio River, and eventually to Washington, D.C. Settlement increased substantially during the subsequent year.

Eliakam Ashton won the contract to construct the building on Crawfordville's Main Street; he finished it in August 1824 at a cost of $295.

In 1825 a contract was issued to Henry Ristine to cut trees and pick up chips from under the courthouse so that "hogs would not find a comfortable place in which to make their beds".

Bunting had served as a colonel in the Confederacy during the Civil War before establishing himself in Indianapolis; General Lew Wallace, who was on the Union side during the War and was a resident of Montgomery County, spoke at the dedication of the cornerstone in 1875.

[9] The cornerstone contains an embedded copper box of memorable items, including the key to the old courthouse and a Henry VIII coin.

[10] The terrain of Montgomery County consists of low rolling hills, completely devoted to agriculture or municipal uses.

Located four miles south-southwest of Crawfordsville,[11] the airport handles some 6400 annual operations, nearly all general aviation (some air taxi).

The council members serve four-year terms and are responsible for setting salaries, the annual budget and special spending.

The judge on the court is elected to a term of four years and must be a member of the Indiana Bar Association.

[18] The county has other elected offices including sheriff, coroner, auditor, treasurer, recorder, surveyor and circuit court clerk.

[18] Each township has a trustee who administers rural fire protection and ambulance service, provides poor relief and manages cemetery care, among other duties.

The Crawfordsville Library was moved to a new location on South Washington Street in 2005 after the old building became too small for the growing collection.